


As Long As I'm With You

by IslanderBib83, lotrspnfangirl



Series: Take Two [4]
Category: Supernatural
Genre: Alternate Universe - High School, Alternate Universe - Teenagers, Awkward Conversations, Bottom Dean, First Time, M/M, Prequel, take two series
Language: English
Status: Completed
Published: 2015-11-13
Updated: 2015-11-13
Packaged: 2018-05-01 09:10:27
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,561
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5200274
Author URL: https://archiveofourown.org/users/IslanderBib83/pseuds/IslanderBib83, https://archiveofourown.org/users/lotrspnfangirl/pseuds/lotrspnfangirl
Summary: <blockquote class="userstuff">
              <p>Dean and Castiel's first time.</p>
            </blockquote>





	As Long As I'm With You

**Author's Note:**

> They are both 17 in this fic, so I am not counting this as underage as it is the legal age of consent.

Dean lay across Cas' bed, their ankles crossed at the end and holding hands between them while they were watching TV together. It was an early summer evening, the two of them eager for school to finally be over for the year, and smiled, rolling onto his side and draping his arm across Dean’s lower stomach, pulling himself closer to his boyfriend’s body. Dean responded instantly, his arms wrapping around Cas' shoulders and holding him tightly, his lips finding the top of Cas' head.

With his lips pressed against Cas’ skin, Dean knew that it was times like these that were his favorite. No one was bothering them, it was just the two of them, like they were the only ones in the world, and Dean couldn’t imagine being anywhere else. He didn’t _want_ to be anywhere else.

Cas turned his head to the side and pressed his ear against Dean’s chest, letting his eyes fall closed as he focused on the warmth radiating into his body from Dean’s. He felt safe, content, and so very loved being in the enclosure of Dean’s arms. It had only been eight months, barely the blink of an eye in the grand scheme of things and yet, Castiel felt like he couldn’t remember what life was before Dean Winchester had plowed into it and he couldn’t picture his life without him.  
Slowly, Cas pushed up onto his elbow, Dean loosening his grip and his arms sliding down to Cas' hips. Their eyes met and Cas felt his heart stutter in his chest. "Dean?" he whispered, licking his lips, his mouth suddenly dry.

"Yes, Cas?" Dean asked and lifted his body a little to be at level with Cas' face. "What's up?"

"I..." Cas exhaled slowly, feeling his cheeks starting to burn and he tore his eyes away, focusing on the small hole in the neck of Dean's t-shirt. His fingers traced small circles against Dean's stomach and he licked his lip again. "I... I love you," he whispered, glancing up after a moment to see Dean staring at him, his eyes wide. Cas' heart skipped a beat.

"Cas," Dean stammered and felt his heart skip a beat. He licked his lips nervously before letting their lips meet in a gentle kiss.

Cas kissed him back, fingers stilling their circular pattern and clenching in the fabric instead. Dean's lips were warm, soft against his own, and Castiel gave a soft moan against them. Dean ran his hand up Cas' arm before cupping his cheek.

Cas broke their kiss, pulling back slightly to meet Dean's eyes again and leaned into his touch. He gave him a small smile, opening his mouth to speak again but realizing there was nothing left for him to say. He felt free, light after his confession, and dove forward again, sealing their lips together once more.

Dean grinned into the kiss. He held Castiel close to him, exactly where he wanted to be. They melted into one another, a mess of lips and teeth and tongue. Then Cas shifted his body, knee falling between Dean's legs and pressing them closer together. He deepened their kiss, hands pressing flat against Dean’s chest. 

Dean’s legs fell open on instinct, slotting their bodies further together. Cas rolled his hips down against Dean’s, swallowing Dean’s small gasp of surprise as his hands slipped from Dean’s chest to his hips, fingers digging into his hip bones as he held Dean down against the mattress. 

Dean opened his eyes a little, staring up at Cas, but closed them again as he let out a low moan, pressing his tongue further into Castiel’s mouth. The heat of their bodies, the press of Cas’ arousal against his own, had Dean’s entire body feeling like it was on fire. 

They had fooled around before, Cas wa starting to know Dean’s body better than his own, and he wanted it, wanted Dean, wanted to show him just how much he loved him and needed him. He swallowed hard, rolling his hips once more as he broke their kiss and leaned back to stare into Dean’s bright green eyes. “Dean…” he whispered, dipping forward to kiss down his boyfriend’s jaw and throat. “I want you so bad.”

Dean’s eyes widened, swallowing audibly and the air between them was thick, hot. Despite his lips feeling swollen from kissing, his mouth suddenly felt dry. Slowly, he nodded, his pulse bounding through his veins. “Okay,” he whispered. 

"Dean..." he whispered against Dean's lips, moving back and kissing down his boyfriend's jaw and throat. "I want you so bad."

Dean swallowed hard and looked at Cas with wide eyes. Despite his lips feeling swollen from kissing, his mouth suddenly felt terribly dry. Slowly he moved his head and nodded. "Okay, " he whispered.

"Are you sure?" Cas held his breath, eyes flicking up to meet Dean's for a moment, watching the small, but sure, nod of Dean's head. "Okay." Cas' stomach fluttered wildly and he reached for the hem of Dean's shirt, slowly pushing his hands up against Dean's stomach and chest, eyes never leaving Dean's own.

Dean closed his eyes and moaned softly, running his fingers back through Castiel’s hair and pulling him closer. “I love you, too, Cas.”

Cas gasped softly, letting the shock of hearing the words returned wash over him and sending heat through every part of his body. With returned fervor, Cas shoved Dean’s shirt the rest of the way up and helped his boyfriend into a sitting position to pull the shirt off from over his head before doing the same with his own. 

As soon as their shirts were tossed to the floor, Dean’s fingers were at the top of Cas’ jeans, fingers popping open the button and working the zipper down. Eyes locked, he then slipped between them and opened up his own jeans, leaning forward to kiss Cas’ neck and shoulder as he pushed Cas down and crawled over him. 

Cas shuddered in anticipation, his skin hot and stomach twisting as Dean lowered his hips, pressing them against one another again. "Dean," Cas whispered, crushing their lips together as his hands trailed down Dean's back and slid underneath the band of his jeans.

Dean's heart was racing, nervous and excited. He felt like he was walking on fire, and yet felt cold, incomplete in some way. He welcomed Cas' lips hungrily, pushing back into Cas’ hands.

Cas let his fingers trail over the globes of Dean's ass, digging in slightly as he pulled Dean down against him, ground up, and swallowed the gasp that fell from Dean's lips. He's never felt like this before, never thought he'd find someone that fit him so perfect, pushed him so hard as Dean Winchester did. He was nervous, afraid of fucking up, afraid of hurting Dean, but there was nothing in this world that could make him want to stop.

Dean clung onto his boyfriend's arms, deepening the heated kiss. There was no going back now, he needed this to happen. His whole body, every single nerve was on edge, ready to explode. Slowly, Castiel pushed against Dean's shoulders, turning them over and pressing Dean down into the mattress. He kissed him once before sliding off of the bed and crossing over to his bedroom door and clicking the lock. He didn't think his dad would bother them, at least not without knocking, but it didn't hurt to make sure. When he turned back around, Dean's eyes were on him and he was slowly slipping out of his jeans.

Dean dared Cas with his eyes alone to get out of his jeans as well. He wanted to undress him with his eyes, take him in completely, but he also wanted to feel him, feel him close, feel Cas' skin on his own. 

Cas swallowed hard, eyes locked with Dean as he moved to his nightstand and pulled out a bottle of KY and a condom, tossing them both onto the bed. Dean's eyes flicked to it quickly then sank back to Cas'. Castiel exhaled, the sound harsh in the silence of the room, and bent to push himself out of the rest of his clothes.

Dean licked his lips in appreciation and pushed off his tight briefs, smiling at Cas softly in a mixture of embarrassment, lust and encouragement.

"God, Dean. You're so perfect." Cas climbed back up onto the bed, the heat from Dean's body hitting him as soon as he got close, and he shivered as he settled over his boyfriend and found Dean's lips once more.

Dean moaned softly into the kiss and ran his hands over Cas' back wanting to feel as much of Cas at once as he possibly could. He tangled one leg around Cas' leg and pressed their bodies together.

Cas let his hands trail down Dean's sides, sliding to his knees to give him enough room to get a hand between them. He stroked Dean's arousal, his own body responding to the sharp intake of breath Dean gave. Cas eyed the bottle of lube and suddenly felt nervous. He swallowed hard, meeting Dean's eyes and hoped he didn't look as scared as he felt.

Dean looked at Cas seeing that he was at least as nervous as he was. He gently cupped his cheek and smiled. "Let's do it." He half whispered. "It'll be okay."

Cas nodded, appreciating the comforting touch and reached for the bottle. They'd never done this before, but Cas would be lying to himself if he denied the countless nights he thought about it or the times he tried it on himself. He clicked open the cap and with a shaking hand, squeezed out a good sized dollop of the cool gel onto his fingers. "Just... Tell me if it's wrong okay?"

Dean nodded. "I will," he whispered. He's tried it before, alone, pretty soon after discovering he was into boys as well as girls. But they had never tried it together and he had no idea what it would feel like with someone else’s fingers, someone he loved, no idea what to expect. He didn't even know if he would be able to say if something was wrong or just awkward because it would be Cas, not himself doing it.

Cas nodded and leaned forward, kissing Dean's lips, then his jaw and the juncture of his throat and shoulder as he slipped his fingers between Dean's legs and past his balls, seeking the heat of his entrance. Dean inhaled sharply and stilled letting Cas do his thing. He looked at the ceiling finding a spot to concentrate on for a bit.

Cas continued kissing across Dean's chest and throat, focusing on the sounds of his breathing for any indication of pain or discomfort. He pressed gently, letting one of his fingers slip into the tight muscle of Dean's body. Dean gasped lightly, then bit his lip. It felt strange, foreign; wrong and oh-so-right at the same time.

"You okay?" Castiel asked, kissing Dean's jaw softly.

Dean nodded dazed and gently cupped Cas' cheek. "More than okay," he half whispered.

Cas smiled and found Dean's lips, kissing him once, twice before Dean's mouth fell open in a soft sigh and Cas pushed forward, slipping his tongue between Dean's lips. He used the distraction of the kiss to start moving his finger, twisting and pushing, slowly stretching the muscle until it was easy to slip a second finger in along with the first. Dean kissed back gently and rocked into Cas' administration.

Castiel took his time opening up Dean nice and slow, pausing once to add another drop of lube to his fingers before slipping three inside. He shifted his weight, pulling back to watch Dean's face as he crooked his fingers and brushed against the tight bundle of nerves. Dean clenched his teeth hard before he gasped in need of air.

Cas smiled as Dean clenched down around his fingers, his eyes blown wide as he met Cas'. "Fuck, Dean, you're so goddamn gorgeous."

"Cas. Oh Cas, _you're_ gorgeous. I love you, Cas," Dean moaned deeply.

"I love you too, Dean," Cas whispered back, slowly withdrawing his fingers. "Think you're ready?"

"I think so, yes. Yes, I'm ready for you." Dean leaned up and softly pecked his boyfriend's lips.

"Okay," Cas smiled at him, stomach flipping as he looked down at Dean. His boyfriend's cheeks were flushed, lips parted in a soft pant as he stared up at Cas, and he felt completely overwhelmed with the amount of love he felt for him right at that moment.

With shaking hands, Cas reached for a condom, tearing it open. He felt himself flush as he took a second to figure out which way it rolled, knowing Dean was watching his every move. Watching Cas calmed Dean more than it made him nervous. Of course he was nervous, this was the first time they went this far; but seeing Cas fumble with the condom, accidentally putting it on the wrong way at first, showed he was at least as nervous.

Cas gave Dean a small smile and finally managed to roll the condom over his length, hissing under his breath at the contact. "Okay..." he said after a moment, looking back up at Dean. "Um, do you want to do it this way? Or... I mean..."

Dean looked at Cas a little confused. "Um ... I ... I would love to see you," he confessed.

"Me too." Cas ran his hands up Dean's legs, arranging them on either side of his hips as he moved forward, leaning over Dean's body. The room was silent, just their mixed breathing, nervous and anticipating the next step. Slowly, Dean shifted his hips up, sending a shock through Cas as the head of his cock pressed against the curve of Dean's ass.

"Okay, just... Tell me if it's wrong, okay? Or if it hurts or feels bad or anything, okay?"

Dean gulped heavily and nodded. "Yes, I will. I'll tell you." He ran his hand over Cas' arms and smiled at him.

Cas exhaled slowly and reached between them, guiding himself carefully to the tight heat between Dean's spread legs. Cas groaned, the sound loud in his ears, as Dean's body engulfed him. Dean arched off the bed at the initial pain and groaned. He lifted his hips a little more, curling his toes as he pushed up. 

Cas stilled, hands running down Dean's legs softly. "Are you okay, baby?"

"Yeah... Yeah, go on," he smiled softly, hands roaming over Cas’ back and arms, focusing on the feel of him instead of the burn.

Cas bit down on his lower lip, his body almost aching to push forward. But... "Maybe I'm doing this wrong... I'm hurting you. I don't want to hurt you, Dean..."

"No, it's... It's the first time, I'm sure it's normal," Dean half whispered, aching for Cas to move.

"Okay," Cas whispered back, exhaling slowly as he pushed forward some more. The drag was slow, and hot, and tight, and by the time Cas had their bodies flush together, Dean's legs were shaking around his waist. Dean was torn between holding his breath and breathing shakingly.

"Dean? Are you okay?" Cas asked softly. Dean nodded quickly, biting down hard on his lower lip. There was no way he wanted to stop this, no way he didn’t want to have sex with his boyfriend, the slight burn be damned. 

Cas rolled his hips slowly, gasping and falling forward against Dean as his boyfriend's body tightened around him. "Fuck, Dean... I'm not gonna last long..." Dean slowly rocked his hips with Cas' movements, groaning as the pain started to turn into something else...

Reaching between them, Cas wrapped his fingers around Dean's length, stroking it back to full hardness. "I love you," Cas whispered, pulling his hips back before sliding into Dean's body again.  
Dean gasped and arched as Cas started stroking him. "Fuck, Cas!" he moaned.

Cas smiled, twisting his wrist around Dean's swollen flesh, glad that his boyfriend was starting to enjoy himself again. "This okay, baby?" he asked, drawing back to slide forward again, biting back a moan at the feeling of Dean hot and tight around him.

"Yes! Yes, that's okay," he husked softly and moved with Cas. Cas smiled, dipping down to catch Dean's lips in a heated kiss as he rocked his hips forward again, trying to get the right angle to hit the sweet spot inside of Dean's body. Dean shifted with him, clenching tight around Cas’ cock, his legs tighter around Cas’ body.

On the next stroke, Dean’s eyes flew open and he gasped against Cas’ lips, hands digging into the back of his neck. “Christ, Dean!” Cas groaned, hand moving faster along Dean’s cock, his own body coiled tight and white hot as he drove into Dean faster. 

“Cas! There!” Dean’s voice was strained, a hot breath against Cas’ lips. 

"I got you, baby," Cas groaned back, his hips snapping forward harder. He moaned, the sound broken and loud, his hand tightening harder around Dean. "Fuck, Dean.. I'm so close... Want you to come with me..."

"Yes, please. I wanna come with you," Dean moaned.

Cas groaned. He felt himself shaking, a white hot heat driving through him and he knew he wasn't going to last much longer. "Dean," Cas whispered, thumb flicking over the tip of Dean's cock before jacking down again, matching in time with his thrusts. 

Dean bucked into Cas' hand, over and over, going faster. "So close..." He moaned as Cas’ free hand tightened on his hips, fingers digging into his flesh. Cas’ hips stuttered, balls drawing up tight as he spilled his release deep inside of Dean. He found the side of Dean’s throat, teeth digging in on a moan as he felt Dean's body tighten around him.

Dean cried out feeling Cas bite him and, _damn,_ he was certainly gonna have bruises on his hip tomorrow. But the feeling of Cas coming inside him certainly made up for that. It felt good, so good. Dean bucked into his boyfriend's hand a few more times before following him closely with his own orgasm.

“Fuck, Dean,” Cas whispered against his skin, kissing over the bite mark gently and soothing away the pain. He let his hands trail down Dean’s sides, holding him close as they collapsed against one another, breathing slowly returning to normal. 

“Yes, exactly,” Dean breathed. He ran his hand over Cas’ back, tracing random patterns with his fingers. He shifted slightly and winced. “Cas,” he gasped lightly. “I… I need you to... um, get out.”

“What?” Castiel asked, looking down at Dean with confusion before realizing what he meant. He felt himself flush. “Oh! Right, shit… I’m sorry.” He lifted up quickly, pulling away from Dean who winced once more, body twisting. “Crap… Did I hurt you?”

“I don’t know. It hurts. But it felt so good. I… “ Dean turned his face away, his cheeks and neck all flushed. He felt embarrassed that he felt pain, he felt horrible for worrying Cas so much because of it, and yet, underneath all that he still felt really good from having moved forward in their relationship. He bit his lips against the burning in his eyes.

Cas stood there for another moment before slipping off of the bed. He slipped out of the bedroom, coming back a few minutes later with a warm wash cloth. Silently, he crawled up beside Dean, running the warm cloth over his body, taking care to wash every part of him with tenderness, leaning down to kiss every inch of skin he could. When he was done, Cas tossed the washcloth to the floor and reached down for the comforter, yanking it up over them and pulling Dean into his arms. He kissed his forehead softly, tangling their legs together. 

“I love you, Dean,” he whispered, looking down to meet Dean’s eyes. “I’m sorry if I hurt you.”

Dean looked at Cas before just pulling him into a tight bear hug. “I love you too. I’m sorry that I’m a whimp. I wish it didn’t hurt... It’s not your fault, Cas! It’s not your fault,” he sniffed and buried his face in the crook of his boyfriend’s neck.

“Dean!” Cas held him tighter, shaking his head. “God, baby, please don’t think that… You’re not a whimp, I promise you that. I… I’ll do a bit of reading…” Cas blushed slightly but pushed away the embarrassment at getting caught looking up things on the computer and having his Dad end up finding out what he was doing. “Maybe I did something wrong. It’s supposed to be good for both of us. We will figure it out, okay?”

“It was good. It was really good,” Dean assured. “I don’t know what wrong with me. I’m sorry.” He kissed Cas' neck reassuringly. “I’ll do some reading too. It’s about both of us, that both of us enjoy it, also afterwards.”

“Absolutely nothing is wrong with you, Dean Winchester. You’re perfect.” Cas curled against his body further, pressing his face into the crook of Dean’s neck and breathing in deep. “I love you so much, Dean.”

“I love you too, Cas. You’re the best boyfriend I could ever have,” Dean whispered softly. “As long as I'm with you everything is good.”


End file.
